In July of 1994, Vanity Fair ran a full-page photograph in its Vanities section of an up-and-coming new actress named Sandra Bullock. Dressed in black, her short hair wet and tousled, Bullock was shot with her hands on her knees, eyes locked with the camera, legs coltishly askew. Above her left patent sandal is that era-appropriate accessory, the ankle bracelet. She was 27 years old, fresh off small parts in The Vanishing and Demolition Man, and was about to break out in a movie called Speed. “They’re gonna have to dispense aspirin before you see this thing,” Bullock told V.F. of the thriller. (“Just call it Runaway Bus,” we translated at the time.) Of her own mien in the films of her career, she appraised: “I’m the quirky, offbeat funny girl!” Funny, indeed: it’s hard not to chuckle at her line, looking back at it after more than 17 years, an Oscar (won from her first nomination), a production company (Fortis Films), and a 2011 Guinness World Record (for highest-paid actress, making $56 million in one year).

Russell Crow, photographed by Sam Jones for the September 1997 issue.

Since its inception in 1992, two years prior to Bullock’s shoot, the Vanities-opener page has showcased Hollywood’s most famous, before they were far along the road to being that way. The page is conceived and executed as the so-called second cover of the magazine, always featuring a single actress or actor. There’s a 24-year-old Ben Affleck in March of 1997, before Good Will Hunting, who said of his modest success at the time, “I’m just happy not to be holding up convenience stores.” There’s Russell Crowe, laying on the beach in a loud, flag-sized tie in ’97. That was on the eve of L.A. Confidential, which was nominated for nine Academy Awards and kick-started his leading-man years, in which he’s received three Oscar nominations and one statue for best actor. And there’s February 2003, when bafta and Oscar nominee Keira Knightley—then a gangly teen whose feel-good Bend It Like Beckham had been an English box-office smash—spoke almost exclusively about her mom. She was 17.

Ben Affleck, photographed by Eika Aoshima for the March 1997 issue.

“More often than not, this is the first time they’ve ever been interviewed, and you get them when they’re a little more relaxed, before they’re guarded,” says senior West Coast editor Krista Smith, who has worked on selecting the actors for the page for 15 of its 20 years, and interviewed and written the piece for most of that time, as well. “I always like to get someone that I really believe in,” she says, and she looks into whether an actor has the kind of “stamina and longevity” that means they’ll make it in Hollywood. And “making it” means, more often than not, they’ll be back—“Keira Knightley started as a Vanities opener, she ended up on a Hollywood cover, then she got her own cover,” Smith says. In other words, she graduated from the “second cover” to the first, as did “Kirsten Dunst, Scarlett Johansson, Natalie Portman . . . I like to say that they’re in the family,” Smith adds.

Keira Knightley, photographed by James White for the February 2003 issue.

As the level of talent stays the same, the look of the Vanities opener has evolved over the years, from the edgier, closer-shot frame of the 1990s to a more overtly nostalgic, pinup vibe in the mid-2000s, to the bright, modern-but-timeless feel of today. In the mid-aughts, contributing editor David Kamp and associate art director Angela Panichi worked together with Smith to conceive of a fresh editorial and visual look for the page, and landed on the 1940s- and 50s-influenced Technicolor dreamscape that first launched in 2006. By contrast, “the lad-magazine philosophy is, if you’re going to put a young ingénue on the cover, she’s gotta look whorish or slutty,” says Kamp. “The idea was to basically say no—it can be sexy, but the emphasis should be more on beauty than promiscuity.” The source materials that Kamp and Panichi combed—the archives of prominent pinup artists Gil Elvgren and Alberto Vargas, as well as W.P.A. propaganda (see Kristen Stewart’s first V.F. appearance for poster influence) and 1950s cheesecake ephemera—had a resoundingly wholesome quality, despite how suggestive they seemed in the era of their inception. “We reviewed archival material that related to Hollywood glamour for the inspiration—Look magazine, Screenland, and Spy were useful references,” Panichi says. “[The subjects’] youth, beauty, and mystery made the Vargas treatment a natural choice.”

Shailene Woodley, photographed by Robert Erdmann for the December 2011 issue.

Today, the Vanities opener is created with a specific look or feel in mind, often dovetailing with what Smith has learned about the actor’s personality from her personal interactions with them, or her estimation of their performances in movies she’s seen on the festival circuit. For Shailene Woodley, who had a breakout turn in Alexander Payne’s The Descendants, Smith felt she had a gamine, Audrey Hepburn–ish quality in person. Based on a rough concept, Smith, fashion and style director Jessica Diehl, and fashion associate Kate Scheyer came up with ideas. “There was a bike concept and a boat concept,” both based on vintage photographs of Hepburn, says Scheyer, who styled Woodley for the shoot. There is an overall look to Vanities, she adds: “The clothes are modern (to an extent—nothing super-trendy), the lighting is bright and contemporary, but there is always a classic, just-bordering-on-retro feel,” she says. In the case of Woodley’s shoot, she’s attired in nautical reds and blues, in an age-appropriate and era-less shorts-and-tank outfit, and seated on a textural coil of rope—a fun nod to the boat, as well as a way to get the length of her lanky frame into the shot. Vanities-opener props like the rope coil are done with a prop stylist who’s been briefed on *V.F.’*s research materials and from bikes to puppies to toweringly soft-swirled ice-cream cones are a whimsical hallmark of the page. It’s “fundamentally upbeat and colorful, with props, with narrative—not [dominated by] a sullen or moody pose,” says Kamp, who credits Panichi’s design and Smith’s casting in making the modern Vanities opener a success. With the actresses, “it’s this great sense of showing womanhood and femininity.”